Dimethyl Sulfoxide → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To dimethyl sulfoxide (2.82 mL, 39.8 mmol) dissolved in anhydrous methylene chloride (5 mL) and cooled to -78° C. was added dropwise oxalyl chloride (2.6 mL, 1.5 equiv). After 10 minutes at -78° C., N-Boc-Phenylalaninol (5.00 g, 19.9 mmol) dissolved in anhydrous methylene chloride (75 mL) was cannulated into the reaction mixture. After 15 minutes at -78° C., the reaction was stirred for 2 minutes at 0° C. and then cooled again to -78° C. Triethylamine (11.9 mL, 4.3 equiv) was added dropwise. After 25 minutes, the reaction was quenched with cooled 10% citric acid (15 mL) and then diluted with additional 10% citric acid (75 mL). Ether (300 mL) was added and the solution was washed with water (5×100 mL), brine, water (5×100 mL), and brine, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (4.22 g).

Provenance & Evidence